Tom Alaimo
Creating Distance
Creating Distance shares inspiring interviews from the best and brightest minds in B2B and Tech Sales. Each episode brings you raw, unfiltered conversations from legendary salespeople, high-performing reps, and forward-thinking sales leaders to help inspire the next generation of sellers. We explore their come-up stories—the early grind, the pivotal moments, the failures, the breakthroughs—and how these individuals created distance between themselves and the competition so you can take what’s real and apply it to your own sales journey. If you're looking to separate yourself from the pack, thi...
Author
Tom Alaimo
Category
Podcast website
Latest episode
Dec 19, 2025
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Episodes
325: A High-Growth Sales Career w/ Todd Busler, Co-founder Champify 28.11.2022 45:09
In this episode, I talk to Todd Busler about his high-growth sales career. He started as a Sales Engineer at SAP, was one of the first reps at Square and then bet on himself as the first GTM hire at Heap. He stayed for 6 years, eventually becoming their VP Sales. He recently cofounder Champify to help create a new pipeline channel for salespeople. This episode of the Millennial Sales Podcasst is s...
324: Vacations, “Dead Zones” and Creating Momentum 18.11.2022 11:17
In this episode, I talk about creating momentum in your sales career and how to treat vacations and "dead times" around the holidays. This episode of the Millennial Sales Podcasst is sponsored by Dooly. As you probably know, my mission is to help sellers become the best versions of themselves at work and in their lives. Well that’s exactly what the team is doing over at Dooly. Dooly is what top-...
323: Justin Welsh, The Minimalist Entrepreneur 31.08.2022 49:23
Justin Welsh is the founder of JW Strategic Advisory. Prior to that, Justin spent a decade in sales and leadership positions. After a few failed efforts, Justin landed at ZocDoc helped to grow it into one of the fastest companies in the world. Justin then took on the role of CRO at PatientPop and spent 5 years scaling them from $0 to $50M and from 1 to 150+ salespeople. Along the way, he’s grown h...
322: What Entrepreneurship Is REALLY Like w/ Will Ballance, CEO at Lavender 24.08.2022 52:28
Will Ballance is the co-founder and CEO of Lavender, a software that helps salespeople write better emails. Prior to that, he he held numerous sales and sales leadership roles. In this episode, we discuss: Will's background as a sales rep Why he quit his job to become and entrepreneur What it's really like running a software start-up Working from Mexico for the past two years And much more... If y...
321: The Story Behind Morgan J Ingram (Throwback) 17.08.2022 52:50
This is a replay of episode 64 with Morgan J Ingram. Morgan J Ingram is on a mission. Inspired by a fate-driven conversation on a Southwest Airlines flight in 2016, Morgan is striving towards his life purpose. His ultimate goal? To become the greatest motivator of all time. If you’re in the B2B Sales world you likely know Morgan as the creator of the SDR Chronicles, a show focused on tips &...
320: Making Sales More Inclusive w/ Leslie Venetz 10.08.2022 53:49
Leslie Venetz is the Founder of Sales Team Builder, LLC and has spent nearly two decades in sales and leadership roles. In this episode, we discuss: Leslie's first sales job How Leslie was closing deals with the Fortune 100 companies Best cold calling tactics How to make sales a more inclusive place If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts? It ta...
319: Tim Dorris, CRO at Stensul 04.08.2022 40:50
Tim Dorris is the CRO of Stensul and has been in sales and sales leadership for over a decade in SaaS. This conversation is a crossover from the Pavilion Podcast. In this episode, we discuss: How Tim got into sales His path through sales leadership and how he got promoted The life of a CRO in a hot start-up If you enjoy the podcast, would you please consider leaving a short review on Apple Podcast...
318: The Story Behind 30 Minutes To President’s Club (And Other Ventures) w/ Nick Cegelski 27.07.2022 52:34
Nick Cegelski is an Enterprise Account Executive at Time by Ping and Co-host of the popular 30 Minutes To President's Club Podcast. In this episode, we discuss: Nick's passion for wrestling and lessons learned His entrepreneurial journey that started in college The early days of Nick's sales career Why he's chosen to go down the path of Enterprise Sales The story behind 30 Minutes To President's C...
317: How To Prospect Into The Enterprise w/ Elric Legloire, SDR Manager at Chili Piper 20.07.2022 43:38
Elric Legloire is and Enterprise SDR Manager at Chili Piper and Co-founder of the SDR Game Newsletter. He's one of the biggest names in the SDR prospecting game right now. In this episode, we discuss: Elric's path from marketing to sales early in his career How the book "Predictable Revenue" changed his career How he got into SDR leadership The difference between prospecting into SMB and Enterpris...
316: Sell Without Selling Out w/ The Legendary Andy Paul 14.07.2022 54:05
Andy Paul has spent decades in sales, leadership and enablement roles. Currently, he is the Host of the Sales Enablement Podcast and author of "Sell Without Selling Out". In this episode, we discuss: How Andy got started in sales selling door to door B2B in the Bay Area Why going against "common knowledge" in sales can help you How to lean into your authentic sales style And much more... If you en...
315: Solo 06.07.2022 16:00
If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts? It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you. Follow The Podcast: Apple/Spotify: Millennial Sales Twitter: TommyTahoe Instagram: TommyTahoe YouTube: TommyTahoe Website: Millennialmomentum.net
314: Talking Career Growth With Rachel Mayes, VP Sales at Nowsta 02.07.2022 49:29
Rachel Mayes is the VP Sales at Nowsta and Board Member at Girls In Tech NY. Previously, she held sales and leadership roles at Samsara, Chariot and Yelp. In this episode, we discuss: How Rachel got into sales post-grad Starting off her career at Yelp Rising through the ranks of leadership Moving to NYC in the pandemic Giving back to help young women in the tech world And much more... If you enjoy...
313: Decide Today To Be A Major Success w/ Ralph Barsi, VP Inside Sales at Tray.io (Throwback) 02.07.2022 40:14
Today's episode is a throwback to my first conversation with Ralph Barsi, VP Inside Sales at Tray.io. So many great nuggets in here - enjoy! If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts? It takes less than 60 seconds, and it really makes a difference in helping to grow this show and find the best guests possible for you. Follow The Podcast: Apple/Spo...
312: From Credit Card Debt To Financial Freedom w/ Jennifer Welsh 01.07.2022 50:18
Jennifer Welsh is the Founder of Money School, which helps demystify the stock market for young investors. Prior to that, Jennifer was the Founder of CultureOps, and held leadership roles at Thrive Market and ZocDoc. In this episode, we discuss: Jennifer's path with credit card debt How she got interested in personal finance Her advice for people beginning to invest their money How salespeople sho...
311: Ethan Carpenter on Moving From Banking To Sales 01.07.2022 35:29
Ethan Carpenter is a Sales Executive at Four Winds Interaction. Prior to that, he was an Area Vice President at FirstBank. In this episode, we discuss: Why Ethan originally got into baking and finance How and why he transitioned into tech sales His biggest hurdles and learning moments How he uses his growth mindset to get better everyday And much more... If you enjoy the podcast, would you please...
310: Hannah Morris on How To Break Through Your Limiting Beliefs 30.06.2022 47:01
Hannah Morris is a Sales and Business Coach to Creative Female Founders. Prior to that, she held sales and leadership roles at Vibe Tickets, Dreamtek and Eventbrite. In this episode, we discuss: How Hannah got into sales Her path through sales leadership Launching her own business and breaking through her limiting beliefs And much more... If you enjoy the podcast, would you please consider leaving...
309: Morgan Buchanan on Transitioning From Ballet Dancer To SDR 30.06.2022 37:01
Morgan Buchanan is a Sales Development Rep at Spekit. Prior to that, she spent 10+ years as a professional ballet dancer. In this episode, we discuss: Her professional dancing career and correlation to sales Why and how she transitioned into tech How Morgan's booking meetings right now And much more.. If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts? It...
308: Chris Orlob, #2 US Employee at Gong, On How To Craft Your Career 19.06.2022 50:38
Chris Orlob is the Head of Multi-Product Revenue at Gong and was Gong's #2 US employee. In this episode, we discuss: Chris's start in sales Launching his own company Joining Gong as employee #2 How to use hard work, skill development and risk tolerance to separate himself And much more... If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts? It takes less th...
307: How To Break Into Tech Sales w/ Drew Piper, SDR at Reward Gateway 19.06.2022 25:27
Drew is a Sales Development Representative at Reward Gateway. In this episode, we discuss: Passing by University to get into sales Starting in Real Estate sales How Drew broke into tech Some of the creative ways he's booking meetings right now And much more... If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts? It takes less than 60 seconds, and it really...
306: Anthony Natoli: Finding A Path To Success, Mental Health and Fulfillment 01.06.2022 51:31
Anthony Natoli is a Commercial Account Executive at Outreach. Prior to that, he held several sales roles at Demandbase and Ethos Lending. He is also one of the top voices in sales on LinkedIn and a co-founder (with yours truly) of the new sales community, The Up & Up In this episode, we discuss: How Anthony got into sales The path of destruction he fell into in his first few years of sales Rock bo...
305: The Playbook For Enterprise Sales w/ Nate Nasralla, Founder at Fluint 01.06.2022 42:24
Nate Nasralla is the Founder at Fluint. Prior to that, he had growth, sales and leadership roles at GAN, Global Startup Studio Network, among others. In this episode, we discuss: Nate's life as a start-up founder A deep dive into how to sell enterprise deals And more... If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts? It takes less than 60 seconds, and...
304: From The School of Hard Knocks to CRO in 10 Years w/ Steve Travaglini, CRO at LinkSquares 25.05.2022 49:08
Steve Travaglini is the CRO at LinkSquares. Prior to that, he was a sales leader at OnShape and Datto, among other companies. In this episode, we discuss: Steve's transition from college football to sales The odd jobs he did before sales and how that transformed his mindset Getting through the ups and downs of sales How he's thinking about hiring during the Great Resignation And much more... If yo...
303: Sales Is Like Dating w/ Jen Allen, Chief Evangelist at Challenger 24.05.2022 52:09
Jen Allen is the Chief Evangelist at Challenger and Host of the Winning The Challenger Sale Podcast. Prior to that, she spent 14 years selling at CEB and Gartner. In this episode, we discuss: How Jen got into sales after graduating from Penn State Jen's struggles with imposter syndrome How sales is like dating And much more... If you enjoy the podcast, would you please consider leaving a short rev...
302: Getting Into Tech With A Unique Background w/ Matt Roberts, Director of Sales Development at Mosaic 19.05.2022 49:08
Matt Roberts is the Director of Sales Development at Mosaic and was formerly running Sales Development at Chili Piper. In this episode, we discuss: How Matt got into sales from a very unique background His leadership philosophy for SDRs What he learned from his time at Chili Piper His obsession with NFTs and Crypto And much more... If you enjoy the podcast, would you please consider leaving a shor...
301: Sales Legend Mark Roberge Tells His Story 17.05.2022 37:17
Mark Roberge is one of the most legendary people in the SaaS sales world. He joined Hubspot as their first sales hire and led them from $0 to $100 million+ and a successful IPO as their Chief Revenue Officer. He is now the Managing Director at Stage Two Capital and Professor at Harvard Business School. In this episode, Mark and I discuss: How he first got into sales & startups Was getting an MBA w...
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